本文希望利用薁類的雙極特性，合成分子間具有偶極-偶極吸引力的3位置、4位置及3,4位置上不同碳鏈的羧酸薁類化合物，以作為吸附在銀表面的自組裝及混合自組裝單層薄膜材料。
第一部份由起始物2-對甲苯磺醯氧酮(B)合成薁的中間物(C)及(D)( 2-氧-2H-環庚﹝b﹞呋喃-3-羧酸甲酯C及8-烴基-2-氧-2H-環庚﹝b﹞呋喃-3-羧酸甲酯(D)，中間物(D)與長鏈溴烷反應，合成8-壬烷氧-2-羰基-2H-環庚﹝b﹞呋喃-3-羧酸甲酯(E)及8-十七烷氧-2-羰基-2H-環庚﹝b﹞呋喃-3-羧酸甲酯(F)，再與乙醛、二乙胺反應合成4-壬烷氧-薁-1-羧酸甲酯(I)及4-十七烷氧-薁-1-羧酸甲酯(J)。
第二部份，再利用正十二醛及正二十醛與1,4氧氮陸圜先形成烯胺類，再與上述合成之化合物(C、E、F)進行[8+2]環加成反應，生成3位置不同長短碳鏈的3-正烷基-薁-1-羧酸甲酯(G、H)及3,4位置分別為短-短(K)、短-長(L)、長-短(M)、長-長(N)的3-正烷基-4-正烷氧基-薁-1-羧酸甲酯。
最後將合成的薁類羧酸甲酯化合物(G~N)經水解，合成最終產物分別為短、長的3-正烷基-1-羧酸薁類化合物(O、P)、4-正烷氧基-1-羧酸薁類化合物(Q、R)及短-短(S)、短-長(T)、長-短(U)、長-長(V)的3-正烷基-4-正烷氧基-1-羧酸薁類化合物。
之後，擬以所合成之最終產物(O~V)為原料，以吸附於銀表面形成自組裝及混合自組裝單層薄膜，利用原子力顯微鏡、反射式紅外線光譜分析薄膜結構，作為判斷薄膜的排列情形是否因薁類的偶極-偶極作用力呈現均勻相的分布？

Making use of the dipolar property of azulene, we synthesize 3-alkyl-azulene-1-carboxylic acids, 4-alkoxy-azulene- 1- carboxylic acids and 3-alkyl-4-alkoxy-azulene-1-carboxylic acids as the material for self-assembled monolayer and mixed self-assembled on silver surfaces.
we start with p-touenesulfonyloxytropone(B) to synthesize the intermediate of azulene, C and D (methyl 2-oxo -2H -cyclohepta[b] furan-3-carboxylate C and methyl 8-hydroxy- 2-oxo-2H- cyclohepta﹝b﹞furan-3-carboxylate D),and intermediate D has been reacted with 1-bromononane and 1-bromoheptadecane to accomplished methyl 8-nonoxy-2-oxo-2H-cyclohepta[b]furan- 3- carboxylate(E), and methyl 8-heptadecoxy-2-oxo-2H- cyclohepta [b]furan-3- carboxylate(F),and then reacted with diethylamine and acetaldehyde to accomplished methyl 4-nonyloxy-azulene- 1-carboxylate(I) and methyl 4-heptadecyloxy-azulene-1- carboxylate(J).
we use dodecanal and isosanal reacted with morpholine to form enamine ,and then reacted with the compounds that the aforesaid compounds (C、E、F), to accomplished two 3-alkyl-azulene -1-carboxylates(G、H),and four different 3-alkyl-4-alkoxy- azulene -1-carboxylates(K、L、M、N).
Finally after hydrolysis we are successful to get two 3-alkyl-azulene-1-carboxylic acids(O、P), two 4-alkoxy- azulene -1-carboxy acids(Q、R), and four 3-alkyl-4-alkoxy- azulene-1- carboxylic acids(S、T、U、V).

1. Abraham,Ulman.;Chem.Rev.1996,96,1533
2.Bigelow,W.C.;Pickett,D.L.;Zisman,W.A.Collid Interface Sci.1946,1,513
3.R.G.Nuzzo.D.L.Allara,J.Am.Chem.Soc.1983,105,4481
4. Ulman,A.An introduction to Ultrathin Organic Films, From
Langmuir-Blodgett to Self-Assembly; Academic Press:Boston,1991.
5.涂明顯,碩士論文,國立清華大學化學系,2002.
6.Ulman ,A.;Eilers,J.E.; Tillman,N.Langmuir 1989,5,1147.
7.Bain,C.D.;Troughton,E.B;Tao Y.-T.;Evall,J.;Whitesides,G.M;Nuzzo , R.G. ;J.Am.Chem.Soc.1989,111,321
8.Nuzzo,R.G.;Dubois,L.H.;Allara,D.L;J.Am.Chem.Soc.1990,112,558.
9.Hickman,J.J.;Ofer,D.;Zou,C.;Wrighton,M.S.;Laibinis,P.E.;Whitesides,G.
M.J.Am.Chem.Soc.1991,113,1128
10..Strong,L.;Whitesides,G.M.Langmuir.1988,4,546
11.Chidsey,C.E.;Loiacono,D.N.Langmuir. 1990,6.709
12.Dubois,L.h.;Zegaski,B.R.;Nuzzo,R.G.;J.Chem, Phys.1993,98,678
13.Chidsey,C.E.D.;Liu,G-Y.;Rowntree,Y.P.;Scoles,G.J.Chem.Phys.1989,91,4421
14.Alves,C.a.;Smith.E.;Porter,M.D.J.Am.Chem.Soc.1992.114,1222
15.Sellers,H.;Ulman,A.;Shnidman,Y.;Eilers,J.E.J.Am.Chem.Soc.1993,115,9389
16.Nuzzo,R.G.;Dubois,L.H.;Allara,D.L.J.Am,Chem,Soc.1990,112,558
17.E.Delamarche,B.Michel,H.A.Biebuyck,C.Gerber,Adv.Mater.1996,8,719.
18.Allara,D.L.;Nozzo,R.G.,Langmuir,1985,1,45.
19.Schlotter,N.E.;Porter,M.D.;Bright,T.B;Allara,D.L.Chem.Phys.Lett.1986,132,93
20.Tao,Y.T.J.Am.Chem.Soc.1993,115,4350
21. Samant,M.G.;Brown,C.A;Gordon,J,G.Langmuir,1993,9,1082
22.陶雨台,自然科學簡訊第十五卷第二期,2003,32.
23.Tao,Y.T.;Pandiaraju,S.;Lin,W.L.;Chen,L.J.Langmuir.1998,14,145
24.Bain,C.D.;Whitesides.G.M.Am.Chem.Soc.1989.111.7164
25.Folkers.J.P.;Laibinis,P.E.;Whitesides,G.M.Lamgmuir.1992,8,1330
26.Siepmann,J.I.;McDonald,I.R.Mol.phys.1992,75,255.
27.Stranick,S.J.; Parikh,A.N. ; Tao,Y.-T.; Allara, D.L. ;Weiss,P.S. J.Phys. Chem.1994,98,7636
28.Shon,Y.S.;Seung.H.Lee,Scott S.Perry,J.Am.Chem.Soc.2000,122,1278
29.Lauterbur,P.C.J.Am.Chem.Soc.1961,83,1838
30.Yasunami,M. ;Miyoshi,S.;Kanegae,N.;Tadase,K.Bull. Chem.soc. Jpn. 1993, 66, 892.
31.Nozoe,T.;Seto,S,;Mastsumura,S.;Murase,Y.Bull.Chem.Soc.Jpn,1962,35,1179
32.Wang,F.;Lai,Y.H.;Kocherinsky,N.M.;Kosteski,Y.Y.Org.Lett.2003,5,995,
33. 游瑞成,有機光譜學,徐氏基金會出版,1998
34.Nozoe,T.;Takase,K.;Kato,M.;Nogi,T.Tetrahedron,1971,27,6023
35.Kice,J.L.;Bowers,K.W.J.Am.Chem.Soc,1962,84,605
36.Nozoe,T.;Asao,T.;Yasunami,M.;H.;Suzuki,T.;Ando,M.J.Org,Chem.1995,60,5919
37.Yasunami,M.;Miyoshi,S,;Kanegae,N.;Takase,K.Bull.Chem.Soc,Jpn,
1993,66,892